Vacation Condo Rentals By Owner In Islamorada, FL

Your own tropical paradise overlooking the fabulous Florida Bay - brthis family favorite is just 67 miles south of Miami! Futura Yacht brClub is a small, gated community with a private marina and braccommodations available for that tranquil tropical getaway you've always imagined. This is an elegant 5th floor 3 bedroom, 2 bath condo large enough for a party of 7, but still stylish, comfortable and affordable. This condo has a private balcony and is located in the tower bldg, just a short elevator ride away from the tennis courts and swimming pool. This condo comes fully equipped with all your vacation comforts in mind. Wireless internet available. Protected dockage is available for boats up to 36 feet with easy ocean access through Snake Creek or Tavernier Creek for just $200 per week. $250 per week during holiday weeks. brIf you need a slip, please request when booking and we will adjust your quote. brVacation Rental License #25-0427

3/2 condo Futura Yacht Club Pool, Dockage, Wifi, dockage, beach

Islamorada, Florida, United States

3

Bed

Bath

6

Sleeps

$155.05

PROPERTY NAME: The Palms #417br79901 Overseas Highway, Islamorada, FLbrbrLOCATION: Oceanside Condominium brbrMINIMUM STAY: 28 Days, All stays must be the whole month(s), No Partial Months AllowedbrbrMILE MARKER: 79.9brbrDETAILS: The Palms of Islamorada is a condo complex consisting of 84 units and is located directly on the Atlantic Ocean. The complex features separate his and hers mini-gyms, heated pool, hot tub, tiki for gatherings and lots of lounge chairs so soaking up the wonderful sunshine. This one bedroom unit has partial views of the ocean and a good view of the Florida Bay. It is perfectly proportioned - large living area and large bedroom and dressing area with separate linen closet and walk-in closet. The kitchen and baths have been updated. You'll be glad you chose this unit for your holiday in the Keys. Bedding is king. This property is professionally managed by Keys Holiday Rentals.brbrSleeping Arrangements: Sleeps 2-3 comfortablybrPrimary Bedroom: King, Ensuite Shower/ Tub CombobrBathroom 2: ShowerbrbrAmenities Include: Community pool and hot tub, Indoor community area/kitchen, gym, Outdoor lounge chairs.brbrActivities: Beach, Swimming, Boating, Offshore Fishing, On Shore Fishing, Paddle Boarding, Museums, Wildlife Reserves, Art, Shopping, Historic Tours and Culinary Adventures.brbrENHANCED CLEANING, DISINFECTION AND SANITIZATION: Our number one priority is the wellbeing and safety of our guests. We have contactless check-ins and check-outs. Our properties are cleaned and sanitized by professionally trained and equipped housekeepers who provide quality service, security and personal accountability. We use CDC housekeeping protocols, approved disinfectants and personal protection equipment. Our properties are private, well maintained, hygienic and sanitized. A whole safe and private space just for you and your family. brbrRESERVATIONS ARE NOT CONFIRMED UNTIL THE REQUIRED CONDOMINIUM ASSOCIATION APPLICATION IS APPROVED.

Updated Unit with Beautiful Florida Bay Sunsets

Islamorada, Florida, United States

Bed

Bath

Sleeps

$396.5

PLEASE EMAIL US WITH ANY QUESTIONS WE ARE HAPPY TO PROVIDE THE ANSWERS ABOUT OUR PROPERTY, OUR RESORT, RESTAURANTS, WATER SPORTS and ACTIVITIES! brWE ARE ONE OF ONLY A FEW LEGAL 7 NIGHT RENTALS IN ISLAMORADA AND THE FLORIDA KEYS -THERE IS A 28 NIGHT MINIMUM RENTAL LAW & ILLEGAL RENTALS ARE SHUT DOWN DAILY- BUYER BEWARE!brCONCIERGE SERVICE -We provide you with as much concierge service as you desire EMAIL US ABOUT OUR SPECIAL SAVING$$$$$$$$$$$$$$brAQUA OCEAN VIEW + MARINA VIEW = AQUAMARINE brCONTACT US FOR BEST DEALS + SPECIALS And SAVE$$$brBEST VIEW + BEST DOCK + BEST LOCATION + 5 STAR AMENITIES brANGLERS REEF BUILDING br ELEGANT TROPICAL ISLAND RESORT + ELEVATORS + LUGGAGE CARTS brDOCK- BRING YOUR BOAT or have a RENTAL DELIVERED TO YOUR DOCK brFREEZER for bait/catch brBEST BEACH FRONT KEYS RESTAURANTS just minutes away brWE ARE ALWAYS AVAILABLE FOR YOUR QUESTIONS br 100% 5 STAR REVIEWS = BEST DREAM VACATION!!!brAMENITIES! AMENITIES!! AMENITIES!!! Private Dock with water and electric + Heated Pool + Hot Tub + Fitness Center + LIghted Tennis Courts + Clubhouse + Huge Locked Equipment Closet with Freezer + FIsh Stations+ Gas Grills + Gated +++ brENDLESS WATER SPORTS & ACTIVITIES: boating, fishing, diving, snorkeling, sport fishing, lobstering, jet skiing parasailing, paddle boarding, kayaking, swim with the dolphins, explore art galleries, shopping....endless opportunities = FUN!!!brCONCIERGE SERVICE - We provide you as much concierge assistance as you desire. WE CAN HELP YOU HAVE A RENTAL BOAT DELIVERED TO YOUR DOCK! NO QUESTION IS TO SMALL!brLOCATION, LOCATION, LOCATION!!! By LAND or SEA we have the BEST LOCATION! We are located in beautiful ISLAMORADA which is widely considered THE PINNACLE OF THE FLORIDA KEYS!!! Islamorada means Purple Island!!! Key West, Key Largo, Marathon and ALL OF THE FLORIDA KEYS are a SHORT DRIVE on the VISUALLY STUNNING OVERSEAS HIGHWAY CONNECTING ALL OF THE FLORIDA KEYS and are easily accessible for lunch or day visits! CONCIERGE SERVICE!!! Please read our 100% 5 STAR REVIEWS!! We are available 24/7 to answer any of your questions. Also, we love helping travelers explore the purple islands of Islamorada, and the Florida Keys. It is our joy to share all of its secrets with our guests.brbr***************************IMPORTANT INFORMATION**************************brAQUAMARINE is ONE OF A FEW LEGAL WEEKLY RENTALS ALLOWED IN ISLAMORADA and ALL OF THE FLORIDA KEYS. Monroe County (The Florida Keys) has a 28 NIGHT MINIMUM RENTAL LAW!!! We are educating traveler's so your Dream Vacation does not turn into a NIGHTMARE! You arrive and NO VACATION because of ILLEGAL RENTAL ACTIVITY! br Weekly Vacation Rental Licenses:brVillage of Islamorada # VR-053 ( Monroe County)brState of Florida # CND5403498br Our licenses PROVIDE YOU with the INSURANCE that WE WILL NOT BE SHUT DOWN BECAUSE OF ILLEGAL RENTAL ACTIVITY!!! brWE MEET THE HIGHEST FIRE AND SAFETY STANDARDS TO PROTECT YOU AND YOURS!!! WE ARE FULLY LICENSED!!!

AQUAMARINE OCEANVIEW+””SPECIAL RATES””+ DOCK+POOL+GYM+SPA+”153”5 STAR REVIEWS!!!

Islamorada, Florida, United States

Bed

Bath

Sleeps

$165.42

Gorgeous 2 bedroom 2 bath condo all on one floor with HEATED POOL, DOCK FOR FISHING, AND OUTDOOR BALCONY. Gated community makes it a perfect getaway for a family for 4 but sleeps 6 to accommodate any short term visitors. Inside our home, you will find stainless steel appliances, a master bedroom with queen size bed with large outdoor balcony! Bathrooms have shower/tub combo and main bath has shower with separate vanity area. Walk in closet. Second bedroom has a full size bed and trundle bed/sofa. Living room has a queen size sofa bed with upgraded memory foam mattress. We would love for you to be our guest for your next unforgettable vacation in the beautiful Florida Keys. Contact Nancy for more details about the condo located at Mile Marker 87.5 on the ocean, guests can be sure to get a true Keys experience! Located within walking distance of local restaurants for the ultimate vacation in the beautiful Florida Keys! Sauna, community room, fitness room, bbq area, grassy/sand oceanfront lounging areas, kayak and storage are just a few of the amenities offered to our guests. Our very own boat/fishing captain lives in our building and will offer our guests a discount for the following services. br He would be delighted to take you and your guests on a boat ride, out fishing for the day, or to the world famous Sandbar for a day of relaxing boating fun. Also available are experts in scuba diving if you are interested in getting certified while on vacation. The possibilities of this vacation are endless! We know the Florida Keys and look forward to sharing with you all of our favorite activities and restaurants.

STUNNING CONDO with BALCONY/POOL in Oceanfront Building in beautiful Islamorada!

Islamorada, Florida, United States

Bed

Bath

Sleeps

$902.3

Summary:brThis spectacular three-bedroom, three-and-a-half-bathroom penthouse unit is located within a luxury beachfront community in Islamorada. The Maison is at the heart of Islamorada with its own 350 feet of private beach and a 150’ pier out over the water. This exclusive, gated resort complex is on the Atlantic side of Matecumbe Key. It is home to white sand beaches, clear waters, and warm weather.brbrThe Space:br*We can accommodate up to 8 guests if two are under the age of 6*brbrThis fully furnished 3-bedroom, 3.5-bathroom condo boasts high-end features and upscale furnishings throughout. The outdoor terrace overlooks an 86-foot lagoon-style pool with breathtaking ocean views and includes a fireplace, grill, and a beautiful outdoor dining area. The living room is the perfect space for family and friends to gather, watch movies, or enjoy board games together.brbrRelax by the pool with ample seating, dining areas, and multiple BBQ options, or enjoy outdoor entertainment with the terrace TV. A hot tub is also available for your enjoyment by the pool area. brbrEach bedroom includes an ensuite bathroom. The impressive master bathroom features a large rain shower, soaking tub, and a spacious double-sink vanity. The other two bedrooms each offer a well-sized bathroom with a shower and a single sink.brbrWe provide all the comforts of home—you won’t need to bring a thing! Enjoy luxury linens and towels, premium toiletries, a fully stocked kitchen, a washer and dryer, and a selection of board games for your entertainment. brbrWhen you're ready to explore, The Maison is conveniently located near various restaurants and activities. You can walk around town or use our beach cruisers. Additionally, stand-up paddleboards, kayaks, beach cruisers, and snorkel gear are available for rent, making it easy to enjoy the surrounding waters and area.brbrThis is an ideal destination for scuba diving, snorkeling, fishing from our private dock, or simply lounging by the pool. Islamorada offers the perfect setting for enjoying the beautiful waters of the Florida Keys. brbrMiami International Airport is an 85-minute drive, and Fort Lauderdale International Airport is about two hours away.brbrPlease Note:brbr**The Maison dock is for pick-up and drop-off only. Nearby marinas offer boat rentals and dock slips.br**A sofa bed is available in the living room.br**A high chair and pack-and-play are available upon request at no additional charge. Please request in advance.br**A recreation package can be added to your reservation for an additional fee. Please reach out for details.brbrGuest Access:brA door code will be provided by our team for a convenient check-in/out experience.

Islamorada Penthouse with Private Beach & Pool!

Islamorada, Florida, United States

Bed

Bath

Sleeps

$697.1

Sunrise Haven is professionally cleaned including all linens and towels. The owners or property manager do not do the cleaning and laundry. brbrIslamorada, Florida, is known as the Sports Fishing Capital of the Florida Keys. The Maison resort property in Islamorada is half way between Key West and mainland Florida. Sunrise Haven, our Atlantic Ocean beach front condo is located near the heart of Islamorada at Mile Marker 80.6 on the quiet, less traveled, Old Federal Highway, not on the busy US-1 Overseas Highway. Walk to great restaurants, the arts district and marinas in Islamorada. The Maison resort property includes 21 condos, in 4 buildings in a U shape around a very large, 86' x 25', resort style pool and hot tub. Enjoy 350 feet of white sand beach. We provide 2 double kayaks, 2 stand-up paddle boards and a kayak cart to aid rolling the kayaks and SUPS to the beach for our guests private usage. The Overseas Highway, US-1, follows Henry Flagler’s famous railroad to Key West that was destroyed in the deadly Labor Day hurricane of 1935. Miami International Airport is an 85 minute drive. Fort Lauderdale International Airport is a 2 hour drive. From Sunrise Haven a visit to Key West is an easy 80 mile, 90 minute drive. “Downtown Islamorada” is home to a number of great restaurants for casual outside, waterside dining or more upscale seafood, chop or steak dinners. You can walk to the Midway Cafe for an outdoor or indoor breakfast or lunch and the opposite way on the Old Hwy to the famous Green Turtle Inn and Restaurant for all three meals. Fishing charters and scuba diving are close by.brbrWhether you are coming to the Keys for a relaxing, restful break from cold weather to lounge around the pool or on the beach, to catch lobster and stone crabs, to go snorkeling or scuba diving, to spend your time fishing the back country for snook, redfish, bonefish and tarpon or to go off shore fishing for dolphin, wahoo, snapper and grouper, Sunrise Haven in Islamorada can be your comfortable home away from home. The panoramic sunrises and moonrises are beautiful from our condo's main balconies, the beach or the pool area. You can also enjoy sunset from our guest bedroom balcony. Our condo is a legal, yearly safety and fire inspected, private rental in Islamorada. Our Islamorada vacation rental license number is 25-0267.br brThe Maison resort property is an exclusive, private gated resort condominium complex located on the Atlantic Ocean side of Upper Matecumbe Key in Islamorada. It has one of the few sand beaches in the Florida Keys. There is no overnight boat dockage or trailer storage available onsite. There is a 155 foot Day Dock from the middle of the beach into the Atlantic available for daytime dockage. Safe Harbor Anglers House Marina, 305-664-5247, at 80500 Overseas Hwy has a nice launching ramp and may be able to store your boat overnight and your trailer. Safe Harbor Islamorada Marina, 305-664-8884, at 80462 Overseas Hwy may also have overnight boat storage and trailer storage. They may be able to bring your boat to the Maison day dock or golf cart you over to the marina. The common areas of the Maison complex have undergone significant recent renovations that includes an 86 foot by 25 foot resort style pool. The 24/7 hot tub looks out over the Atlantic. The beach area has a gas fire pit, lounges, umbrellas, Adirondack chairs and hammocks. The pool area includes updated lounges, tables and umbrellas. There is a beachside Summer Kitchen with a Chickee covered eating area and two 30 inch gas BBQs. You can relax in a hammock, a lounge or at an umbrella shaded table and read a book on the beachside terrace. Snorkel or swim from the beach or the ladder on the day dock platform, fish from the day dock or have fun with our 2 kayaks and 2 stand-up-paddle boards for your private use. Only our condo supplies Stand-Up-Paddle Boards for our guest's usage. We also have some fishing equipment in the parking area storage closet for use on the day dock. Since the equipment is used by guests we cannot guarantee how good the equipment has been maintained. Please try to keep saltwater out of the tackle box. If you buy hooks, sinkers, etc. feel free to leave the excess in the tackle box. Please rinse all equipment including the fishing poles and reels with fresh water after fishing.brbrOur 3 bedroom, 3 full bath multilevel condo is located on the upper two levels of the three story building #3 for added privacy. It has two sunrise ocean/beach/pool facing balconies and another sunset balcony off of the upper floor guest bedroom. Only 2 condos have west facing balconies. All three bedrooms have room darkening window treatments. The upper level contains the master bedroom/bath, the first guest bedroom/bath, and full laundry room. The master bedroom has a wet bar/mini-kitchen with refrigerator, coffee maker, electric tea kettle, walk-in closet, hotel style safe, sunrise, ocean facing balcony and a huge master bathroom with a large jetted tub, separate shower area and double vanities. The upper level guest bedroom has two double beds, a small exterior deck with nice views of sunset and accesses the second full bathroom. The lower level has the open dining area, kitchen and great room with a wet bar, wine cooler and a wall mounted HDTV with DVR, DVD and stereo system. The northeast wall of the great room is two sets of sliding glass doors that open onto the balcony with a relaxing seating area for 6 adults and a glass top table with 6 chairs for outdoor dining. The lower level second guest bedroom has a queen bed with access to the third full bathroom. The kitchen has granite counter tops, tile back splashes, quality appliances, wine cooler and an eat-in/bar area with stools. The kitchen is stocked with all necessary small appliances, cookware, serving pieces, cutlery, etc. All bedrooms have HDTVs, cable boxes and room darkening window treatments. You can nap at any hour of the day.brbrSunrise Haven has the X-1 Comcast Cable system with voice remote activation and XFI residential Internet access. You do not need to know the channel number, you just speak into the remote ESPN or ABC or NBC or a movie name and the cable box will respond to the HD channel.brbrMost of our high season rentals are Saturday to Saturday but the weekly rental can be any 7 consecutive days depending upon the season. Sunrise Haven can accommodate 6 adults & NO children or 4 adults & 2 children or 2 adults & 4 children. We cannot accommodate more than 6 adults which includes teenagers.brbrNeed baby gear during your stay We have some baby gear that is available to our guests. brThis includes a full sized crib, high chair, and a couple of pack-n-plays. We do not have enough to supply both of our vacation rental properties in Islamorada, so check with us first We have set up an account with BabyQuip to help our guests with obtaining baby stuff to make their vacation easier and safer.brbrRent cribs, car seats, strollers, toys and more from BabyQuip! As seen on Shark Tank, BabyQuip offers clean, sanitized, and safe baby gear in Islamorada. Visit Sunrise Haven’s unique link https://www.babyquip.com/a/wst21v to make a reservation.brbrIt is likely the only disappointment you will experience at Sunrise Haven is having to depart at the end of your vacation stay. Many of our guests return yearly, some for a month or more, but most for a week. You can join our group of loyal guests.brbrIf you are looking for a weekly Islamorada vacation rental property that can accept boats overnight, please look at Sunset Reef, our bay side 4 bd, 4 1/2 ba private estate at MM 76, www.vrbo.com/809744 or www.HomeAway.com/809744. We also have a Park City/Deer Valley, Utah 4 bd, 4 1/2 ba vacation rental home, www.vrbo.com/206330 or www.HomeAway.com/206330.

Sunrise Haven - Maison 306 - Beach, Pool, Hot Tub, Kayaks, SUPs & Day Dock

Islamorada, Florida, United States

Bed

Bath

Sleeps

$305.31

This spacious two bedroom, two bath condominium overlooking the ocean is located on a quiet 12 acre private gated community. Includes a 30 foot boat slip in a protected marina with direct access to the ocean. Eat in kitchen with breakfast bar open to living area that looks out over the water. Expansive patio for open air dining or lounging. Main bedroom has an ocean view, opens to screened patio, a king sized bed, private bath with soaking tub and walk in shower. The split floor plan design provides a private additional bedroom with a spacious bathroom. Ideal for remote workers, retirees wishing to spend winter in a warm, sunny locale or families looking for an adventurous escape. Large heated community pool and hot tub. Lighted tennis courts. Onsite boat ramp. Club house features a large community room and full gym. Outdoor covered dining area with picnic tables, a gas grill, and ice machine.

Ocean Harbour Condominium is an Oceanfront Fisherman's Paradise in Islamorada

Islamorada, Florida, United States

Bed

Bath

Sleeps

$663.2

.Oceanfront Maison #303 - Maison is a premier gated oceanfront complex in the heart of Islamorada. This prime oceanfront three bedroom, two bath flat unit offers an open concept living and dining room with ocean views, an expansive kitchen with an island and bar seating, and large screened in porch overlooking the Atlantic. The master suite offers breathtaking ocean views, a spacious walk-in closet and a bathroom with a shower and jacuzzi tub that will make you feel like royalty. With a state-of-the-art pool, hot tub, spacious lounge area, tiki hut, beach and observation pier. Two kayaks are provided for you to enjoy the expansive Atlantic..brbrIf booking more than a year in advance current prices may not reflect annual cost of living increase. brMany of our guests' re-book the same property on an annual basis. No reservation is confirmed until you speak with us. brbrVR# 24-0142brbrPlease note: before proceeding with your booking, kindly review the following information. This property is managed by a local Islamorada rental company, Freewheeler Vacations. Payments for your vacation rental will be made thru Freewheeler Vacations. You will also see a charge from VRBO which covers their booking service fee which is already included in the total cost. We prefer payments via personal check or eCheck. However, if you opt to pay by credit card, a 3% convenience fee will be applied to your rental. You will receive the Freewheeler Vacations Vacation Rental Agreement via email, which must be signed before your arrival. All future correspondence will be made through Freewheeler Vacations.

Experience paradise at Oceanfront Maison Matecumbe 303 in beautiful Islamorada!

Islamorada, Florida, United States

Bed

Bath

Sleeps

$244.24

Futura Yacht Club #205 - This charming condo is located in the Futura Yacht Club community, located at mile marker 88.5 on the bay side in Islamorada. The unit comes fully furnished with a full kitchen, dining room, large living room with sleeper sofa, expansive balcony with great views of the Florida Bay and the community's two tennis courts, along with two bedrooms, both with en-suite bathrooms. All you'll need is your toothbrush and a swimsuit, and you're all set for a fabulous Florida Keys vacation. The Futura Yacht Club HOA charges- onsite-$150 per trailer and $50 per boat fee. These fees will not show up on your rental agreement, as the fees are collected upon check in at Futura Yacht Club. brIf booking more than a year in advance current prices may not reflect annual cost of living increase. brMany of our guests' re-book the same property on an annual basis. No reservation is confirmed until you speak with us. brVR-24-0333 Per Islamorada's vacation rental ordinances for weekly rentals 2 people per bedroom are allowed, and 2 additional guests if under the age of 6.brPlease note: before proceeding with your booking, kindly review the following information. This property is managed by a local Islamorada rental company, Freewheeler Vacations. Payments for your vacation rental will be made thru Freewheeler Vacations. You will also see a charge from VRBO which covers their booking service fee which is already included in the total cost. We prefer payments via personal check or eCheck. However, if you opt to pay by credit card, a 3% convenience fee will be applied to your rental. You will receive the Freewheeler Vacations Vacation Rental Agreement via email, which must be signed before your arrival. All future correspondence will be made through Freewheeler Vacations.

Charming 2-bedroom condo in Islamorada with pool access and ocean views.

Islamorada, Florida, United States

Bed

Bath

Sleeps

$246.11

Beacon Reef 404 - Beautiful two-bedroom two baths, condo with everything that you need for a perfect relaxing vacation. Balcony access off your living room and master bedroom that overlooks the newly remodeled pool and jacuzzi as well as the beach and ocean. The complex is oceanfront and has amazing views of the Atlantic. Some additional amenities: chairs and tables on balcony, printer, tiki hut by pool, and undercover parking. brIf booking more than a year in advance current prices may not reflect the annual cost of living increase. brMany of our guests' re-book the same property on an annual basis. No reservation is confirmed until you speak with us. brPlease note: before proceeding with your booking, kindly review the following information. This property is managed by a local Islamorada rental company, Freewheeler Vacations. Payments for your vacation rental will be made thru Freewheeler Vacations. You will also see a charge from VRBO which covers their booking service fee which is already included in the total cost. We prefer payments via personal check or eCheck. However, if you opt to pay by credit card, a 3% convenience fee will be applied to your rental. You will receive the Freewheeler Vacations Vacation Rental Agreement via email, which must be signed before your arrival. All future correspondence will be made through Freewheeler Vacations.

Charming 2BR condo in Islamorada with pool, hot tub, and beautiful views.

Islamorada, Florida, United States

Bed

Bath

4

Sleeps

$246.32

Welcome to your stunning 2 bed/2 bath “Keys Vibe” condo in the heart of Islamorada—also known worldwide as the Sport‑Fishing Capital of the World . Immerse yourself in barefoot‑luxury with: 28 day minimum rental required. brbrProperty Highlightsbr • Spacious living: Two comfortable bedrooms and two full baths—perfect for families or friends.br • Resort-style amenities: Dive into the pool, energize in the gym, melt stress away in the sauna, or unwind at the club house.br • Private pier: Ideal for sunrise coffee, evening cocktails, or casting a line.br • Truly Keys ambiance: Salt‑sprayed air, swaying palms, relaxed lifestyles.brbr Prime Islamorada LocationbrbrYour retreat sits centrally in Islamorada—just minutes from top attractions and activities.brbr⸻brbrThings to Do NearbybrbrDrawn from trusted Florida Keys and Islamorada guides.brbr Fishing & Boatingbr • Charter epic sport‑fishing trips—Islamorada’s world‑class fishing scene is unmatched .br • Explore reefs by boat, snorkel shipwrecks, or relax on local sandbars, including the popular Islamorada SandBar .brbr Marine Encountersbr • Theater of the Sea: Swim with dolphins, sea lions, sharks—or just enjoy animal shows and boat rides .br • Visit Robbie’s Marina to hand-feed tarpon—an unforgettable, Instagram‑ready highlight .brbr State Parks & Naturebr • Wander through Windley Key Fossil Reef Geological State Park to see fossilized coral and explore nature trails .br • Kayak or hike around Indian Key and Lignumvitae Key State Parks, stepping into rich history and lush native foliage .br • Chill at Anne’s Beach, with calm shallow waters, lovely boardwalks, picnic spots, and even kiteboarding .brbr Culture & Museumsbr • Explore the History of Diving Museum, featuring vintage helmets, old‑school diving gadgets, and ocean lore .br • Learn your way through Florida Keys history at the Florida Keys History & Discovery Center and more local museums .brbr Art & Shoppingbr • Stroll through the Morada Way Arts District, especially lively during the monthly Art Walk .br • Discover handmade art and souvenirs at Rain Barrel Village, with its iconic giant lobster sculpture “Betsy” .brbrLocal Flavors & Treatsbr • Sample fresh seafood, lively bars, local craft beer and innovative burritos at Village Square stops like Bad Boy Burrito .br • Don’t miss key‑lime pie at the Blond Giraffe Key Lime Pie Factory .brbr⸻brbrRelax & Unwind Ideasbr • Enjoy serene afternoons at your condo pool, sauna, or pier—escape the world and soak in the Keys lifestyle.br • Sip cocktails at your clubhouse with new friends, or toast the sunset as pelicans glide overhead.br • Jump on your bike or rent e‑bikes to cruise along the Keys Overseas Heritage Trail .brbr⸻brbrStay with Us for:br • Easy access to fishing charters, snorkeling, diving, and sandbar adventures.br • Cultural richness—from art galleries and museums to friendly bars and local breweries.br • Resort‑style comforts and prime location for exploring Islamorada’s vibrant spirit.

Paradise in the Heart of Islamorada.Come relax and have the time of your life!

Islamorada, Florida, United States

Bed

Bath

Sleeps

$634.83

Welcome to paradise! This beautiful three bedroom, two and a half bath end unit condominium sleeps 6 people. Master bedroom has a king bed with direct access to the water front balcony. Second bedroom has a queen bed and the third has two twin beds. Brand new flat screen HD TVs in living room, master and queen guest! Gourmet kitchen has granite countertops, stainless steel appliances and a great selection of cookware and utensils. Open floor plan with wet bar and formal dining room. Enjoy your morning coffee or afternoon cocktail with the gentle ocean breeze on the wonderful screened in water front balcony. This unit is the model for all of Bay Harbour and is professionally decorated and furnished.brbrThe condo includes all linens and is equipped with a full washer and dryer. Also included is the use of a 50-foot boat slip in a protected harbor with four-foot control depth. The large screened in balcony looks directly at your boat slip. There is immediate bay access and quick ocean access via Channel Two and Channel Five bridges. Fish cleaning stations, shore power and water are also on the slips. A marina is located across the harbor with gas, diesel and bait.brbrPrivate gated community with a large heated pool, jetted spa, two lighted tennis courts, clubhouse with fitness center. New stainless gas grills are conveniently located at the clubhouse for grilling your catch! brbrIslamorada is conveniently located 90 minutes from Miami and Key West. During your visit you can feed the tarpon at Robbie’s, enjoy a spectacular sunset at the Lorelei or swim with the dolphins at Theater of the Sea. brbrIslamorada is the “Sport Fishing Capital of the World”. Tarpon, bonefish, permit, mahi mahi, sailfish and sword fish abound in the tropical waters surrounding Islamorada. Flats fishing or blue water offshore fishing options are at your fingertips with Islamorada having the biggest fishing fleet in all of the Keys! At Bud n Mary’s you will find a great selection of deep-sea charters. Or if you prefer the backcountry, visit Worldwide Sportsman for a variety of different guides. brbrSo whether you want to fish, snorkel, dive or just sit by the pool and relax, this condo has something for you. br

Elegant Bay Harbor Condo with 50 Foot Boat Slip, Heated Pool, Hot Tub, and Gym

Islamorada, Florida, United States

3

Bed

Bath

6

Sleeps

$306.81

Experience Islamorada like a local in this 3-bedroom condo. This superb property features 2 queen beds and 2 bunk beds, perfect for families or groups of friends. With amenities like WiFi, AC, and a washing machine, guests can relax and unwind in this peaceful retreat. The 2 bathrooms come equipped with a hairdryer and shower for added convenience. There is also an outdoor area- and a BBQ are also a plus. A great place to call homebase while you're away, we hope you enjoy your stay.

Charming 3-bedroom condo with WiFi and AC in delightful Islamorada

Islamorada, Florida, United States

Bed

Bath

Sleeps

$638.73

Oceanside Isle - Oceanview Isle is a hidden gem located in a gated condominium complex on Long Key, a quiet location conveniently located between Islamorada and Marathon. This 3/2 end unit has a large private patio with breathtaking views of the ocean, a boat slip that will accommodate boats up to 34' and access to a shared pool. Located on the first floor is an open concept kitchen and living room with unobstructed views of the ocean. Off of the living room is a private balcony with seating and a grilling area. Also located on the first floor are two bedrooms, one with a queen bed and one with two twins, and a shared bathroom. The second floor features a master ensuite with a king bed and a large patio with stunning views of the turquoise waters of Long Key Bight and State Park.brIf booking more than a year in advance current prices may not reflect annual cost of living increase. brMany of our guests' re-book the same property on an annual basis. No reservation is confirmed until you speak with us. brbrPlease note: before proceeding with your booking, kindly review the following information. This property is managed by a local Islamorada rental company, Freewheeler Vacations. Payments for your vacation rental will be made thru Freewheeler Vacations. You will also see a charge from VRBO which covers their booking service fee which is already included in the total cost. We prefer payments via personal check or eCheck. However, if you opt to pay by credit card, a 3% convenience fee will be applied to your rental. You will receive the Freewheeler Vacations Vacation Rental Agreement via email, which must be signed before your arrival. All future correspondence will be made through Freewheeler Vacations.

Experience coastal bliss at Oceanside Isle, a spacious 3-bedroom condo in Long Key.

Islamorada, Florida, United States

Bed

Bath

Sleeps

$400.84

Welcome to your slice of the Florida Keys at the Bay Harbour Condominium Complex in Islamorada. This bright and spacious 2-bedroom, 2.5-bath condo offers the perfect mix of comfort, style, and laid-back island living—ideal for a relaxing getaway with friends or family.brTucked inside a quiet, gated community, you’ll feel away from it all while still being close to everything that makes the Keys special.brThe kitchen is fully equipped with granite countertops and stainless steel appliances, making it easy to cook up your fresh catch or a casual dinner at home.brInside, the condo is bright, spacious, and thoughtfully designed with a clean coastal aesthetic. The open living area is filled with natural light and flows seamlessly onto a private screened-in balcony—ideal for morning coffee, evening cocktails, or simply enjoying the warm ocean breeze.brThe fully equipped kitchen features granite countertops and stainless steel appliances, making it easy to prepare anything from a quick breakfast to a full seafood dinner after a successful day on the water.brBoth bedrooms offer privacy and comfort, each with its own en-suite bathroom. The primary suite includes a king bed, balcony access, a large walk-in closet, and a spa-style bathroom with soaking tub, walk-in shower, and double vanity. The guest suite features a queen bed, pool views, and plenty of storage—perfect for couples or friends traveling together.brStep outside and enjoy beautifully maintained tropical grounds, a large resort-style pool, hot tub, and plenty of space to relax in the sun. Start your day with a workout in the fitness center or a match on the tennis courts, then cool off poolside.brBringing a boat You’re in the right place. Your private boat slip (with power & water) is just steps away, with quick access to both the bay and ocean—perfect for fishing, sandbars, or sunset cruises. Fish cleaning stations and grilling areas make it easy to enjoy your catch at the end of the day.br Resort-Style AmenitiesbrBay Harbour offers a full suite of amenities designed to enhance your stay:br• Heated/chilled pool & jetted hot tub br• Tennis courts & fitness center br• Clubhouse & beautifully maintained grounds br• Outdoor grills & fish cleaning stations br• Covered parking plus guest parking brAfter a day of fishing or exploring, clean your catch and enjoy a relaxed evening grilling by the pool as the sun sets over the water.

Just a Few Friends - Ocean View and Bring your Boat!

Islamorada, Florida, United States

Bed

Bath

Sleeps

$1433.51

Welcome to your dream getaway at Coastal Cove Villa! Nestled in the heart of downtown Islamorada, this spacious 4-bedroom, 4-and-a-half-bathroom abode offers the perfect blend of comfort and luxury for your vacation retreat.brbrAs you step through the front door, you'll be greeted by a warm and inviting atmosphere, where relaxation meets style. The open-concept living area boasts plush sofas and modern decor, providing an ideal space for lounging and catching up with loved ones. Whip up your favorite meals in the fully equipped kitchen, complete with stainless steel appliances and ample counter space, perfect for preparing delicious feasts.brbrWhen it's time to unwind, retreat to one of the four cozy bedrooms, each thoughtfully appointed with comfortable furnishings and soft linens to ensure a restful night's sleep. With 4 and a half bathrooms, there's no need to worry about sharing space – everyone can enjoy their own private oasis.brbrStep outside to the private patio area and soak up the sunshine as you sip your morning coffee or enjoy a leisurely al fresco dinner under the stars. And if you're looking to explore the area, you're in luck – Maison Residence is conveniently located near a plethora of attractions, from stunning beaches to vibrant shopping and dining destinations.brbrWhether you're seeking a relaxing retreat or an adventure-filled escape ,this is the perfect home base for your next vacation. Book your stay today and start making memories that will last a lifetime!

Experience luxury at Coastal Cove Villa, a 4-bedroom retreat in beautiful Islamorada!

Islamorada, Florida, United States

Bed

Bath

Sleeps

$719.4

Welcome to paradise at Maison Matecumbe in Islamorada! This beautiful 3-bedroom, 3-bathroom townhome offers an unforgettable stay with breathtaking ocean views that greet you each morning. Designed with relaxed coastal elegance, the open-concept living space flows seamlessly into a fully equipped kitchen, perfect for whipping up a fresh catch or preparing a leisurely breakfast before a day in the sun. Each bedroom is its own private retreat, complete with comfortable furnishings and serene decor to ensure restful nights.brbrJust a few steps outside, indulge in the community's private beach or unwind by the resort-style pool surrounded by swaying palms. When you're ready to explore, you're perfectly positioned to experience Islamorada's world-famous fishing, diving, and vibrant dining scene. Whether you're seeking a peaceful escape or an adventure-filled vacation, this townhome at Maison Matecumbe is the perfect setting for your Islamorada getaway.

Maison 308 Seaside Cove: A stylish 3-bed condo in Islamorada with stunning views and pool

Islamorada, Florida, United States

Bed

Bath

Sleeps

$324.81

Summary:br2/2 Bay harbor condo with stunning Marina and Ocean views!brbrThe Space:brEscape to the breathtaking Gulf View Retreat in the highly coveted Bay Harbor community! Prepare to be enchanted by this hidden gem, nestled on the pristine shores of Lower Matecumbe Key in Islamorada, eagerly awaiting your arrival for your next unforgettable vacation. Discover the allure of Bay Harbor, a captivating four-building complex offering a wealth of amenities, including a shimmering community pool, tennis courts, an invigorating exercise room, and a marina. As a distinguished guest of this remarkable unit, you will enjoy exclusive access to an 18k boat lift, ensuring your cherished vessel remains secure throughout your stay. Please note that trailer storage is available offsite as it is not provided within the community. Embrace the prime location of this community, granting you seamless access to both the majestic ocean and the serene Florida Bay, perfect for indulging in all manner of boating adventures. Just moments away, you'll find the renowned Robbie's, an outdoor marketplace and restaurant, famed for its captivating Feed the Tarpon experience. We eagerly anticipate the honor of welcoming you to this extraordinary piece of paradise!brbrStep into this exquisitely appointed second-floor condo, where the allure of two beautifully adorned bedrooms and two bathrooms awaits you. Revel in the breathtaking views of the immaculate marina and the vast expanse of the ocean that grace every corner of this home. The master bedroom beckons with its generous walk-in closet, ensuite bathroom, luxuriously comfortable king-sized bed, and direct access to a private screened-in patio, where you can bask in the serenity of the surroundings. The guest bedroom is equally enticing, boasting its own private ensuite bathroom, as well as a queen-sized bed and a twin bed, ensuring a restful night's sleep for every guest. The fully equipped kitchen stands ready to cater to your culinary desires, providing all the essentials needed to craft a delicious home-cooked meal away from home.brbrWhen you step outside the front door, a world of adventure awaits at the marina, where in mere minutes, you can set sail to prime fishing grounds teeming with tarpon and other impressive trophy fish. For a change of pace, venture into the backcountry, where acclaimed snook fisheries await your skillful cast. Immerse yourself in the wonders of the nearby coral reefs, where divers can revel in the mesmerizing sight of graceful sea turtles gliding through the water, accompanied by vibrant schools of fish darting among the living corals, creating an unparalleled spectacle that epitomizes the very essence of the Keys.brbrGulf View Retreat offers you an invitation to a realm of tranquility and natural wonders, where stunning views, impeccable accommodations, and unmatched experiences converge. Allow yourself to be captivated by the allure of this coastal haven, where each moment is a testament to the extraordinary beauty of the surrounding landscapes. Your idyllic escape begins here, at Gulf View Retreat, where memories are made and dreams come to life. brbrbrThis home is managed by The Florida Keys Rental Store. For recommendations or things to do while in the keys, we have all the information you could need. Over 20 years in the business, we know what it takes to make your trip the best one yet!

Gulf View Retreat @ Bay Harbor

Islamorada, Florida, United States

Bed

Bath

4

Sleeps

$184.39